


History on Repeat, But It's Not a Time Machine

by RowanWhitethorn333



Category: Gilmore Girls
Genre: F/M, I don't hate Logan but I don't think he's right for Rory, Post AYITL, literati fluff
Language: English
Status: In-Progress
Published: 2020-10-05
Updated: 2020-12-02
Packaged: 2021-03-08 04:00:42
Rating: General Audiences
Warnings: No Archive Warnings Apply
Chapters: 3
Words: 3,211
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/26845534
Author URL: https://archiveofourown.org/users/RowanWhitethorn333/pseuds/RowanWhitethorn333
Summary: Rory has turned into her mom. Single, jobless, and most importantly, pregnant. How will her mom react? How will Logan react? Will he help her raise the child? Or will he become Christopher? (hint: yes). And how about Jess? Is he just a friend? (hint: no). Or will he be the Luke to her Lorelai? (what do you think?) Please R&R! Feedback (good or bad, just not mean) would be greatly appreciated!
Relationships: Luke Danes/Lorelai Gilmore, Rory Gilmore/Jess Mariano
Comments: 2
Kudos: 21





	1. Chapter 1

**Author's Note:**

> A/N: Hi everyone! Thanks for being willing to give this story a try. It takes place after the final 4 words of AYITL (which was pretty terrible in my opinion). Just an FYI, this chapter will contain alternating perspectives of both Rory and Jess. Thank you, and please R&R! Constructive criticism would be appreciated!

_"_ _Mom?"_

_"_ _Yeah?"_

_"_ _I'm pregnant"._

"What?" asked Lorelai.

"I'm pregnant," Rory repeated softly, suddenly unsure. Her mom would supportive, right? There was no way that she would get angry.

"Could you repeat that? Because I swear I heard you say that you're pregnant. My hearing must be deteriorating in my old age, because there is absolutely NO WAY that my responsible daughter, the "princess" of Stars Hollow, could POSSIBLY be—".

"MOM!" Rory exclaimed, causing a few passersby to turn their heads towards to where the Gilmore girls were sitting in the gazebo. She was shocked. She knew her mom might be surprised, but this? This was not what she was expecting. "Please, just let me explain—".

"Explain?" Lorelai scoffed, unconsciously raising her voice. "Oh, there is nothing to explain. I mean, obviously I know how all the birds and bees works. And there is NOW WAY that you can explain why you have been sleeping with an engaged man!"

"Mom!" Rory begged, near tears. Each word struck harder than the last, throwing even more salt into the already open wound."Please keep your voice down!"

"Oh, don't worry". Lorelai said quietly. "I just have one more thing to say to you. This is the only thing I have ever told you to not follow my footsteps in. This is the only mistake I have ever told you not to make. And you went and made it anyways".

"I'm not a child anymore! I'm an adult!". Rory was frustrated at this point. How could Lorelai say these things? Didn't she understand better than anyone how hard this was?

"Then you better start acting like it!"

Rory stood up quickly, tears streaming down her face. "I thought that you would support me when I needed you the most. I guess I was wrong". And with that, she ran down the steps of the gazebo and sprinted away.

* * *

Jess was wiping the tables in the diner, but paused when he looked out the window and saw Rory run away from the gazebo, leaving her mother behind. He watched as Lorelai sat there for a few minutes, before wiping her face, and with a determined expression, walk towards the diner.

"Hey, uh, Luke?" Jess said.

"Yes?" asked Luke gruffly, writing on his notepad.

"You might want to check on your fiancé... I mean, wife." Jess corrected, still a bit hurt he hadn't been invited to the midnight elope. "I think she and Rory just had a fight."

At this, Luke quickly looked up, just in time to see Lorelai walking in with a fake smile plastered on her face, which Luke immediately saw through. With a quick nod of acknowledgement at his nephew, he strode over to Lorelai, and whispered something that only Lorelai could hear. Immediately, Jess could see her face start to crumple, and he watched as Luke put his arm around her and lead her towards the stairs.

"Jess, you're in charge," Luke said. "I might need a while".

Jess nodded. As soon as he heard the door of the apartment upstairs close, he yelled, "Caesar! You're in charge! There is something I have to do".

Without waiting for acknowledgement, Jess was out of the door, towards the once place he knew Rory would be.

* * *

Rory sprinted across the town until she reached the bridge. She sat down on the edge, then let out a sob, finally allowing herself to let go of all the worries and frustrations she'd been carrying around for the past week. She cried because of how stupid she'd been, she cried because her mother was right, she cried because she was scared of how everyone else would react. As she continued to cry, she got too caught up in her misery to hear the footsteps approaching from behind her.

Suddenly, a hand gently touched her shoulder, causing her to jump. Slowly, she raised her head. And came face to face with a very concerned-looking Jess.

Seeing the worry etched on his face just caused her to cry even harder, because she didn't deserve his worry. In typical Jess fashion, he didn't say anything. He just sat down and put his arm around her, offering whatever comfort he could. He knew that Rory would talk when she was ready.

"How did you know where to find me?" Rory asked. "Actually… how did you know I needed to be found?"

"I was wiping the tables in the diner, and I saw you and your mom in the gazebo. Then you suddenly ran off. A few minutes later, Lorelai came in, looking really upset. Luke took her upstairs to the apartment, so I left Caesar in charge and came to find you. And in answer to your first question... I just... know you, I guess," Jess said, seemingly a little embarrassed by that last sentence.

"Thank you," Rory sniffled, and leaned in closer to Jess. He hugged her tighter, and they sat there in silence.

They stayed like that for a few more minutes, Rory appreciating the fact that Jess wasn't pushing her to explain what had happened. Not that she had expected him too. Jess was…. Jess. He always seemed to know what she needed. In that moment, she realized how much she had missed him. Missed... this. She had missed his comfort, his steadiness. She had missed knowing that he would always be there for her. Because she knew he would be. No matter what.

It was this last realization that caused her to say, "Jess?"

"Yeah?"

"I'm pregnant."


	2. Chapter 2

**Summary for the Chapter:**

> How does Jess react to the new turn of events, and will Lorelai change her opinion?

Jess froze, his mind replaying the words over and over again. _"I'm pregnant. I'm pregnant. I'm pregnant"_.

He knew it had to belong to that douche, Huntzberger. Not that he'd been a creepy stalker and keeping up with Rory's love life. In fact, he would probably prefer to not have known. Unfortunately, Jess had walked in on Luke and Lorelai's conversation when he visited a few months back, and Luke had been going on a rant about how Rory could so much better than that "cheating, rich scumbag". Jess was very tempted to stand up and walk away, just like he always did when he was a teenager. But then Jess took one look at Rory's tearful, frightened, and yet slightly hopeful face, and he knew that he couldn't. Even if he wanted to, he wouldn't be able to bring himself knew that no matter how much pain, how much heartache this would cause him, he would stay. Because despite how many times they'd hurt each other over the years, he loved her. He would always love her.

"So... how did your mom take it?" Jess asked, choosing a safer question to ask. "Wait, I'm sorry. That's a stupid question."

Rory let out a small chuckle. "It's ok. But as you can see, not too well."

Jess sat there silently, waiting for her to elaborate.

"I knew she wouldn't be ecstatic. I know she's always wanted more for me. Wanted me to do more. But I figured that she'd be supportive, ya know? Instead, she totally freaked on me. It's like she's become Emily Gilmore the Second". Rory started crying again. And Jess's heart broke when Rory whispered, "I want my mommy."

* * *

She knew how childish it sounded, and she hated it. But she couldn't help it. No matter how grateful she was to Jess for being here for her, without even an ounce of judgement, she couldn't help but wish her mom was here.

"It's just... my mom is supposed to understand," Rory managed to get out, as she tried to calm herself down again. "She's supposed to know how hard this is. How I feel, knowing I made such a stupid mistake. She's supposed to know what it feels like when everyone including your mom turns against you!"

Jess started to rub her back, helping her calm down. "She'll get over it. I think it just took her by surprise. As you said, she just wants more for you. She wants you to live the best life you can." Rory took a deep breath, finding comfort in Jess's words.

"Besides," Jess added a few second later. "Not everyone has turned against you. I'm here. And I promise I'm not going anywhere."

With these words, Rory threw herself into Jess's arms, holding him tight, almost as if to make sure he couldn't leave. She'd forgotten how much she relied on him. How comfortable, how right it felt to be here, with him. Then she remembered. Right. She was pregnant. With another man's child. She quickly pulled away, immediately missing the warmth of Jess's embrace. Wiping her eyes, she took a deep breath, steeling herself.

"You're right. Mom is just surprised. I'm going to try talking to her again. Hopefully she's calmed down a bit, and it will go better this time around".

At hearing her words, Jess stood up, offering his hand. Rory grabbed it, and he gently pulled her up. He squeezed her hand lightly, before letting go. "Remember, I'm here".

Rory smiled shyly at him, and led the way towards the diner.

* * *

Jess knew he was playing with fire. When Rory had hugged him earlier, it had been almost impossible for him to let go. Every few minutes, he had to remind himself, " _She's pregnant with someone else's child. She doesn't love you_ ". But oh was it hard to resist pulling her to him and kissing her senseless. Truthfully, regardless of the fact she was with child, it would still feel like the most natural thing in the world. Suddenly Rory stopped in front of him, causing him to snap out of his thoughts. They stood in front of the diner door, and Jess saw Rory take a deep breath. He stepped forward, and put his hand on her shoulder. "It'll be fine. I promise".

Rory nodded, and stepped forward, the bell jingling as the door opened. 20 faces immediately snapped up to look, and a hush fell over the diner, Jess resisted the temptation to roll his eyes. It seemed like this place would never change.

Lorelai was sitting at the counter, drinking coffee, and when she realized the diner had fallen silent, she turned. For a few seconds, they just stared at each other, with everyone in the diner looking back and forth between them like they were watching s tennis match.

Jess leaned close to Rory and whispered in her ear, "Maybe you guys should go upstairs for some privacy".

She nodded, and tilted her head towards the stairs, signalling her mother. Lorelai gets up from her seat and walks to the stairs, her daughter following behind.

"Ok! Show's over!" Luke yelled from behind the counter. Slowly, the sound of chatter returned to the diner. Jess walked behind the counter and grabbed the coffee, about to go walk around and give refills.

"Jess," Luke said quietly from next to him.

"Yeah?"

"Do you know whats going on?" Luke asked, with a very worried expression on his face.

Jess hesitated for a moment, before saying, "Yes. But... it's not my place to tell you. I'm sorry."

"Could you at least tell me if it's something I need to worry about?"

"I guess it depends on your perspective..."

"What is that supposed to mean?!"

Jess opened his mouth to reply, but before he could, Lorelai yelled from upstairs, "OH I'M SORRY, HOW DID YOU EXPECT ME TO REACT TO THE FACT YOU'RE PREGNANT WITH AN ILLEGITIMATE LOVE CHILD?"

The entire diner fell silent. Jess cursed under his breath, and ran past a gaping Luke and headed up. He got to the top, and threw open the door just in time to hear Rory say, "I don't understand why you are acting like this!"

Lorelai responded, " Because I don't know you anymore. You aren't the daughter I raised".

Jess saw Rory standing in front of her mother, tears streaming down her face, and he quickly strode over and pulled her behind him, almost as if he could stop the hurtful words from reaching her. He faced Lorelai, and said in a deadly serious voice, "I would stop right now if I were you. Both of you are currently overwhelmed by the situation, and if you continue, you will both say something you regret. Especially you, Lorelai. We may have never been friends, or heck, even friendly, but I know you well enough to know that the last thing want is to become your mother. But at this rate, you can give Emily Gilmore a run for her money."

Jess turned to Rory. "C'mon," Jess said tenderly. "Let's go back to the house. I doubt this stress will be helpful for the baby".

He gently nudged Rory towards the door, with Lorelai's shocked face being the last thing he saw before closing the apartment door.


	3. Chapter 3

**Notes for the Chapter:**

> Hi guys. Well, I have basically no excuses for how long it took me to update this. Other than the fact school is kicking my ass currently. But I still shouldn't have taken this long. Thank you guys sooo much for being patient, and I promise the next update won't take this long. Also please review. It'll inspire me to update faster ;D

Rory felt numb. She knew her mom wouldn't be ecstatic about her news; but she didn't expect that reaction. She was stuck in her thoughts, and oblivious to the world around her. Quietly, she allowed Jess to lead her back to the house by the hand, too empty to do anything but follow.

Her mom had been mad before. She had been pissed when Rory slept Dean. She had been even more angry when she dropped out of Yale, and had been disappointed in the actions that had followed (Seriously, what _had_ she been thinking, stealing a yacht?).

But _NEVER_ had her mom acted like this. Like her daughter wasn't even her daughter anymore. Furthermore, Rory now needed her mom more than ever.

Rory had been able to handle the consequences Dean situation, and even the multiple consequences of dropping out. But... she didn't know anything about motherhood. She didn't know the first thing about being pregnant. Hell, she couldn't even find her own underwear! How was she supposed to raise an actual living creature?

Jess stopped, startling Rory out of her reverie. She had been too lost in her thoughts to realize they'd made it back to her house already.

"Do you have the key..." Jess trailed off as he turned his face toward her, his eyes softening at the tears welling up in her eyes.

Rory nodded, and with shaking hands, fished the key out of her pocket, and handed it to Jess. Taking the key, he released her hand to unlock the door. He immediately grabbed Rory's hand again and ushered her inside.

The door slammed shut behind them, and for a few seconds, they just stood there, drowning in the silence and emptiness surrounding them.

Rory couldn't help but think about how weird it was to stand here, this place she called home, and for the first time in her life, feel like she didn't belong there. This realization was the final nail in the coffin that broke the dam inside of her, and heavy, heartbreaking sobs started to make its way out of her. Never had she felt so alone.

* * *

Jess stood there next to Rory in the foyer, not knowing whether he should break the suffocating silence. But then, Rory started sobbing, harder then he'd ever heard her cry. The sound broke his heart. Immediately, he pulled her into his arms, kissing the top of her head.

"Shhh... it's ok. I'm here. I'm here", he reassured her.

Rory grabbed Jess's shirt tightly, holding onto it like a lifeline. Jess continues to hold her and whisper comforting words, until she eventually calmed down.

When her cries subsided into soft sniffles, Jess drew back slightly.

"Why don't you go lie down for a while? You might feel better afterwards."

Rory gave a slight nod, and slipped out of Jess's arms and headed to her bedroom. Jess followed her, with a hand resting on her lower back.

Rory walked into her room, and immediately flopped onto the bed.

Jess reached for the blanket that was gathered at the foot of the bed, and gently tucked her in. Then he leaned down, placed a soft kiss on her forehead, and said quietly, "Sweet Dreams."

He walked over to the door, glancing back once. She was already asleep. He closed the door gently behind him, and went to sit down in the living room. 

* * *

For the past hour, Jess had been seated on the couch, frantically writing in his notebook. He had been suffering from writers block, but it seemed that after spending time with Rory, he had found inspiration once more. 

Just then, a knock on the door shook him out of his own little world. Jess put down his notebook and pen, and strode to the door. He looked through the peephole, and was surprised to see Lorelai standing there. 

A bit reluctantly, Jess opened the door, and for a few second, the two of them just stood there, awkwardly, looking at each other. 

Finally, Lorelai broke the silence. "Hey, Jess. Um, is Rory here? I really need to talk to her."

"She's sleeping," Jess said coldly. "Besides, I think you've said enough."

Lorelai looked down in shame. "Yeah, I deserved that."

Jess said nothing, and leaned against the doorway, waiting to see if Lorelai would say anything else. 

"I just want to apologize to her," Lorelai blurted out, looking at Jess pleadingly. "I messed up. I REALLY messed up. And I have to fix this. So please, can I come in?"

"Fine," Jess said, stepping aside. "But if you upset her one more time, you're out of here."

Lorelai nodded, and walked in. "I never imagined I would need permission to go into my own house. Let alone from Jess Mariano," she muttered under her breath. 

Jess almost smirked at that. "I bet you never imagined you would treat your daughter like you did either."

Lorelai sighed. "I deserved that too." She went to the living room and took a seat on the one-person couch in the corner. Jess went back to the sofa, grabbing his pen and notebook off the table, and continued writing. 

* * *

Lorelai twiddled her thumbs, unsure what to do. She looked at Jess out of the corner of her eye. He kept writing, pretending not to take note of the awkwardness. 

They sat there, until suddenly a sound from further inside the house broke the silence. 

"Jess?" Rory softly called out. 

Immediately, Jess stopped what he was doing and went to check on her. Lorelai decided to follow him. 

She stopped in the doorway, and watched as Jess crouched next to the bed. 

"Hey," she heard Jess say quietly. "Do you feel any better?"

Lorelai saw the lump in blanket move, as if Rory was shrugging her shoulders. 

Jess sighed. "Your mom is here, and she wants to talk to you." Rory visibly stiffened at this. "Don't worry; I'll be right outside if you need anything, ok?"

Rory gave a small nod. Jess leaned over and placed a gentle kiss on her temple, then headed towards the door. On his way out, he shot Lorelai a warning look that said, "You upset her, and you will regret it."

Lorelai nodded in acknowledgment. Truthfully, she was glad that Rory had else someone looking out for her, especially since she herself should've been doing that. 

Lorelai stepped into the bedroom, and looked at her daughter. "Hey."

"Hi."


End file.
